A Boy's First Period free porn video

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A Boy's First Period by Unknown Paul never dreamed that his high school biology assignment would lead to his first taste of femininity. He first fell in love with all things feminine when his sister, Karen, introduced him to bikini panties. Karen also taught him the finer points of feminine hygiene and what is like to have a period. It all started when Paul came home with a biology assignment. He was to write about the workings of the female reproductive system. He went to his sister for help. "Gee, Karen, I don't know anything about this stuff. Pul-leeeeze help me!", Paul begged. Karen hesitated. "Well, Paul, There is a way I think you can help yourself.", she said. "What's that, Karen?" "I believe in learning by doing, so your class will begin this following Saturday while mom and dad are away.", she said. "What do you mean?", Paul asked. Staring Paul straight in eyes, Karen stated, "You'll see. These are the rules...Period!" On Saturday, Karen presented Paul with a dozen pair of bikini panties. They were all new, and were all in different fabrics, styles, and colors. She also gave him 3 new bras, all in an A cup size that would fit him without stuffing. Paul always had slightly swollen breasts since puberty. "Now Paul", She insisted, "the best way for you to imagine what a girl feels like between her legs is for you to wear girl's underwear." Reluctantly Paul agreed to give it a try. Little did he know that she also was about the shave his legs, and shave his patch of pubic hair into feminine triangle. After shaving Paul pulled on a feminine lace pair of bikini panties. His head spun as he felt the delicate underwear between his legs. His cock responded by stiffening. "That doesn't look very feminine", Paul joked. Karen helped him tuck his cock back between his legs. She then had him pull on a pair of her tight Chic jeans. She then helped him snap a bra in place. He filled it out nicely. After that he pulled on an oversized girl's camp shirt. Paul couldn't believe it. He had a flat girlish crotch. It really looked like he had a pussy. The straps of his bra could be faintly seen under shirt. Paul and Karen sat around watching television together until about 2 o'clock. "So, Paul, what does it feel being a girl?", Karen asked. Paul answered, "I really love it." "Looks like you're ready for phase 2.", she said. "What's that?", he asked. Karen giggled. "Your period!" Taking her by the hand they went off to the garage and got into her car. Together the drove to a supermarket down the street. "Why are we here?", Paul asked, nervously. With a naughty gleam in her eye, Karen answered, "You have to buy some Kotex and and some Tampons. Here's your shopping list." She handed him a piece of paper. The feminised boy unfolded it to find the words "Kotex Deodorant Maxi Pads" and "Tampax Junior Tampons" written on it. They got out of the car and walked to the market. "Don't be nervous. This is what you're going to have do from now on", Karen whispered to him. Nervously Paul bought the feminine hygiene items, wondering if anyone noticed his bra straps or his flat girlish crotch. Returning home they went to Karen's bedroom. Paul removed his girl's jeans. Shivering with anticipation, Paul opened the box of tampons. Karen took out the little instruction leaflet and unfolded it. Karen pointed out the diagram of the female reproductive system in it. Pointed to Pauls crotch she said, "This is where your vagina and ovaries are." "It's okay, Paul. I know this is new for you, but its natural for a girl your age. You'll have to get used to this, because a period will be a part of life from now on", Karen said. "Okay Karen. Will you show me how?," Paul asked. "Sure!", she said. Together they each took a tampon out of the box. "Here's how to do it, Paul", Karen explained as she inserted hers into her pussy. Gingerly, Paul unwrapped his, and inserted it into his rear. "Wow, does that feel neat.", he giggled. Next they each took out a Kotex. As Karen placed hers in her panties, Paul positioned the sanitary napkin in his panties. He then pulled the panties up his legs. The feel of the sanitary napkin on his balls and cock felt so good that his head begun to swim. The room swirled and his breath deepened and quickened as he came in his panties, coating his Kotex with cum. "Good girl," Karen said. "Now I have your next present," she said She handed him a denim mini skirt. This was Paul's first skirt. Trembling he pulled it up his legs and buttoned it around his hips. Admiring himself in the mirror. he gasped at how good felt and looked. He kissed his sister on the cheek, and thanked her for his lesson. They spend the rest of the afternoon watching TV. Every few hours they both got up to go change their tampons and Kotex. After a few times Paul got to insert Karen's tampon into her, and she did the same for him. The next day, still wearing panties, a Kotex and tampon, and his girl's clothes Paul wrote his report. When Monday morning arrived they got dressed for school. Paul wore boy's jeans and shirt on the outside, but underneath he had on his panties and his bra. Karen chuckled as he dutifully changed his tampon before dressing and then placed his Kotex securely in his panties. She didn't have to tell him to do it now. "You know, Paul", his sister informed him, "that you'll have to carry a few tampons and Kotex to school in your backpack, as your period will last through Tuesday." Paul asked, "But when will I change them. What if I run out?" "Don't worry. I'll tell you when to change them." As luck would have it, Paul did run out. "Help, Karen! Pul-leeze get me a Kotex and a Tampon from the girl's room", Paul begged. "No, Paul. Remember, this is now a part of your life. You have to be prepared for your period." Karen gently insisted that Paul sneak into the girl's room and buy a Kotex and a Tampax both from the vending machines. Checking that the coast was clear she snuck him into the girl's restroom. Paul put a quarter in each machine and bought his feminine protection. Paul turned to leave. "Where do you think you're going?" Karen asked. Paul stuttered. "You're here, so you have to change change your feminine protection here in the girl's room.", Karen stated flatly. So, there Paul was. A boy wearing bikini panties and a bra, in the girl's restroom, changing his Kotex, and inserting a tampon up his 'pussy'. What a turn-on! Again the room spun and he came in spurts. After that Paul wore bikini panties regularly, and had to wear pantyliners every so often. "Just to be prepared", Karen explained. Of course, Karen and Paul had our their together every month. When Paul moved away from home, those events become a fact of life with him. Now he always wears panties and bras. Every month you'll see him in a grocery store buying his Kotex and Tampax tampons in preparation for his period. He never misses one! By the way, Paul got an A on his report!

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Boys Food! As a site that looks quite bad, I was surprised to see that boysfood.com actually has good content... I still prefer to subscribe to a premium site and have everything in HD, from the content to the site's design, but I also know that not many of us are able to just throw our money at premium pornography, which is why I am reviewing this free porn site.If you visit this site and mistake it for an ad, you should not feel bad, because honestly, that is how shitty Boys Food looks like....

Free Porn Tube Sites
1 year ago
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WhatBoysWant

What Boys Want! What else would boys want more than; to grab those tiny soft nipples they see everyday popping out of see-through tops and perhaps savour them inside their mouths, to probably see their crushes making out/ naked/ masturbating, or rather to slide under those tiny skirts mature pretty ladies wear to work among other fuckin' naughty fantasies that hardly ever see the light of day unless, of course, you check out whatboyswant.com. This sex bombshell is packed up with lots of...

Free Porn Tube Sites
1 year ago
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Femboys

Reddit Femboys, aka r/Femboys! Welcome back to all my subreddit lovers. We are here to talk about yet another subreddit that I find incredibly addictive, and it is called r/FemBoys/. Now, if you are not really into that theme of feminine boys, then you might want to browse through other subreddits instead. Here you will only have the lovely boys who enjoy dressing feminine and doing all kinds of other shit.I think that one cannot get confused with a subreddit like this one. You will either love...

Reddit NSFW List
1 year ago
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Boys Cant Play Basketball

Note: The author encourages unauthorised reposting, sequels, and blatant plagiarism of this work. BOYS CAN'T PLAY BASKETBALL By Wyrdey "Ready to lose, girlies?" Brad sneered. While the other members of the school's female basketball team glared at him, I just grinned. We were going to win this game, I was quite certain of that. That's why I'd convinced the others to challenge these cocky jocks to a match. We were so tired of Brad and his buddies making all those...

1 year ago
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Boys Will Be Boys

Nan was looking forward to the evening with "the boys". Tim and Tom were twin 14 year olds and Nan was their godmother. She had met Sharon, their mother, while they were in college, later on had been Sharon's bridesmaid and, obviously, she knew the boys since they were both born. Tonight was Sharon and her husbands Jim's fifteenth wedding anniversary and Nan had volunteered to be the boys baby sitter. Nan arrived at the Miller house just after seven in the evening and when the door opened...

3 years ago
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Boys Home Chapter 1

Introduction: Following the lives of several boys/men in a group home in California. Richie place his small, slender hand on Edgars thigh, they locked eyes and they both leaned their heads in for a kiss. Their lips locked and Edgar slipped his tongue in Richies mouth. Their tongues danced around in each others mouths until Edgar finally pulled away. Edgar was sixteen, he had a lean, muscular build and a tan from the San Diego weather he enjoyed so much. He was tall for his age, he stood about...

2 years ago
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Boys Brigade Femucation

Boys Brigade Femucation Chapter 1 - Discovery From a very young age I was aware that I am a pretty boy and have experienced the pleasure of being dressed in my elder sister's clothes for the entertainment of family members - although not when my father is at home. My sisters think it is great fun and my mum goes along with my aunt who is the main protagonist in making me look so sweet and girly. From around the age of four, I enjoyed these sessions, however I became aware that it...

2 years ago
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boysrsquo first times 2 out of teen sex party

Ryan knew Owen was gay long time before Julia’s exclusive party. Did he, himself, knew he was attracted to boys prior to making out with Owen in fuzzy light and weed smoke?It started only as silly spin the bottle they arranged mostly for a cheap thrill. But once the luck made them a pair, he just couldn’t get enough of it. Owen was a petite redhead, always well-dressed, a little too serious for his age, liked by almost everyone that knew him. And Ryan… well, he was just some average dude....

3 years ago
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A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

Crossdressing
4 years ago
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A Day of Firsts

A Day of Firsts by Kathy Nelson [email protected] (c):Kathryn Nelson, 1998 It was one of those hectic work periods where I was putting in 70 to 80 hours a week. You know, when there's no time for anything else in your life except the job. But, thank god the rush was over and it looked like things were going to calm down. Friday night had come around and I was going home at a decent hour. I even had the whole weekend off and I was ready to celebrate. Well, more like...

2 years ago
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An Afternoon of Firsts

The bar was crowded for the big football game. Standing room only. I was alone but hoped to find another regular to watch the game with. I ordered a beer and resigned myself to a disappointing spectacle. A good game was much more enhanced when watching with a familiar face or two. Halfway through my beer, I see Jim walk in. Jim was a guy a frequently chatted with and we really hit it off. He was the perfect guy to watch the game with. I flagged him over, shook hands and told him "Looks like...

Seduction
2 years ago
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4th bi experiencemany firststrue story

My 4th Bi experience happened that night of my 3rd experience. I'll never forget it was on a Saturday,Sept 24 1983. I was 16. It was 7:16 pm when I looked at the clock for what seemed like the millionth time. My parents were down the street at another neighbors house. I was sitting in my bedroom wondering what time I should go over to Charles house the anticipation was killing me. Earlier that day he asked if I wanted to come over tonight but what time should I go? I had occasionally looked out...

3 years ago
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A Vacation of Firsts The Conclusion

Eric watched with unblinking eyes as the tiny panties revealed a small but erect cock hidden underneath, and that was another first for him. The stunning woman before him had just pulled her panties down and revealed a cock and he was not repulsed. Tonya's head was bowed in shame with this act. To her, it was like showing off a birth defect. Eric responded by placing his fist under her chin and gently raised it up and looked her in the eyes. He gave her a warm smile and then removed his boxer...

Trans
3 years ago
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Boys they make the best girlfriends

 Do you like the scent of a freshly mowed lawn? I do. But even so, it has to be right. By that I mean it needs to be a warm day with temperatures in the seventies. I also prefer if the sun is out; shining brightly down upon the neighborhood and all those who live in it. There’s just something about the smell; you inhale deeply and it smells like summer. Of course it always smells better when it’s your own yard and not one of a neighbor. When you’re out pushing that mower around your own...

Love Stories
3 years ago
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Boys are ordered to jerk off by a woman in front o

Boys are ordered by a woman to jerk off in front of her.(Everyone in this story is over the age of 18.) The fitness test would be the last step before I would be accepted into the sex training academy. We were issued exercise clothes. I was given running shoes, shorts, and t-shirt with the logo of the academy on it. The instructor was a slim blond named Jackie with long hair and a nice tan. Her assistant was Liz, a slim brunette with long hair and a prefect hour glass figure. They were both...

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